CN103228725A - Novel polymeric thickening agent free of acrylamide fragments, method for the preparation thereof, and composition containing same - Google Patents
Novel polymeric thickening agent free of acrylamide fragments, method for the preparation thereof, and composition containing same Download PDFInfo
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- CN103228725A CN103228725A CN2011800575323A CN201180057532A CN103228725A CN 103228725 A CN103228725 A CN 103228725A CN 2011800575323 A CN2011800575323 A CN 2011800575323A CN 201180057532 A CN201180057532 A CN 201180057532A CN 103228725 A CN103228725 A CN 103228725A
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
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- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
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- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
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- C08F2/00—Processes of polymerisation
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
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- A61Q1/02—Preparations containing skin colorants, e.g. pigments
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
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- A61Q1/14—Preparations for removing make-up
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A61Q19/00—Preparations for care of the skin
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/06—Preparations for care of the skin for countering cellulitis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/002—Preparations for repairing the hair, e.g. hair cure
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
Abstract
The invention relates to a composition including an oil phase, an aqueous phase, at least one water-in-oil emulsifying system in the form of a positive latex, characterized in that the composition includes a straight, branched, or cross-linked anionic polyelectrolyte, including: a) a non-zero molar proportion of monomer units from acrylic acid in free or partially salified form; and b) a non-zero molar proportion of monomer units from the acid of formula (I): CH2=CH-C(=O)-O-[CH2-CH2-C(=O)-O]n-H (I), where n is a number greater than or equal to (1) and less than or equal to (5), in free or partially salified form. The invention also relates to a method for preparing the same, to a polymer powder, and to the use thereof as a thickening agent for cosmetic or pharmaceutical compositions.
Description
Theme of the present invention be novel polymerization anionic thickener, its preparation method with and as the purposes of thickening material and/or emulsifying agent.
The thickening of water is undertaken by mixing all types of hydrophilic polymers (no matter they are synthetic or natural origin) therein usually.
In the polymkeric substance of natural origin, quite be extensive use of xanthan gum or guar gum.But they have the traditional drawback of natural product, i.e. quality and price volalility.
In hydrophilic synthetic thickening agent, the most widely used is powder or from the polymkeric substance of reversible inverse latex form.With regard to chemical structure, they are the acrylate homopolymer of the form of free or partially salinated particularly; The homopolymer of free form is synthetic by precipitation polymerization usually, and is powder type; For the homopolymer of the form of partially salinated, they prepare by precipitation polymerization or by inverse emulsion polymerization usually.For example, disclose from reversible inverse latex in publication number is the european patent application of EP1010708A1, wherein acrylate homopolymer is with the form salinization of ammonium salt or monoethanolamine salt.But the thickening power of the polymkeric substance of this first kind is not exclusively satisfactory, because the existence of nitrogenous base, their bad smell has limited their application in cosmetic industry.Publication number is that the european patent application of EP017025A1 discloses as the vinylformic acid of photographic film layer and the multipolymer of acrylic acid dimer.Publication number is that the German patent application of DE102009014877A1 discloses the 2-acrylamido-1-methyl propane sulfonic acid that is used in the cosmetic industry and the multipolymer of propyloic acrylic ester.
The inventor attempts to develop and has than the good thickening power of the acrylate copolymer of prior art and do not have the thickening polymer of the shortcoming of bad smell aspect.
According to first aspect, a composition that theme is the inverse latex form of the present invention, it comprises oil phase, water and at least a invert emulsion system, it is characterized in that it comprises straight chain, side chain or crosslinked anionoid polymerization ionogen, and this anionoid polymerization ionogen comprises:
A) monomeric unit that produces of the vinylformic acid by the form of free or partially salinated of non-zero molar ratio and
B) monomeric unit that produces of the mixture by the acid of the acid of formula (I) or formula (I) of non-zero molar ratio
CH
2=CH-C(=O)-O-[CH
2-CH
2-C(=O)-O]
n-H (I)
Wherein n represents more than or equal to 1 and is less than or equal to 5 number, and described acid is the form of free or partially salinated.
Term " inverse latex " is meant the water-in-oil emulsion of at least a polymkeric substance.
Term " side chain polyelectrolyte " thereby be meant when the non-straight chain polyelectrolyte with side chain dissolves in water obtains the state that highly tangles, the very high viscosity of generation under the low rate of change gradient.
Term " crosslinking polymerization ionogen " is meant the non-straight chain polyelectrolyte of three-dimensional network form, but its water insoluble be water-swellable and therefore obtain chemical gel.
In the definition of inverse latex as defined above, term " salinization " is meant that it relates to an alkali metal salt, for example sodium or sylvite.
The polyelectrolyte composition of described inverse latex can comprise a crosslink unit and/or a chain unit.
In composition as defined above, " water-in-oil " (W/O) emulsification system constituted or is made of surfactant mixtures by single tensio-active agent, and condition is that described tensio-active agent or described mixture have the HLB value that enough low being enough to causes water-in-oil emulsion.Can mention for example sorbitan ester, for example SEPPIC company is with Montane
TMThe sorbitan oleic acid ester that 80 run after fame sells, SEPPIC company are with Montane
TMSorbitan isostearate that 70 run after fame sells or SEPPIC company are with Montane
TM83 NOFABLE SO-992 of running after fame and selling.Also can mention the sorbitan ester of some many ethoxylation, for example SEPPIC company is with Montanox
TMThe dehydrated sorbitol mono-fatty acid ester of five ethoxylations that 81 run after fame sells or SEPPIC company are with Montanox
TMThe sorbitan isostearate of five ethoxylations that 71 run after fame sells.Also can mention by poly-(isobutenyl) succsinic acid or its acid anhydride and between the molecular weight that produces of condensation be 1000 to 3000 polyester, the Hypermer that sells of Uniqema company for example
TM2296, or last, and molecular weight is 2500 to 3500 segmented copolymer, for example the Hypermer of Uniqema company sale
TMThe Simaline that B246 or SEPPIC company sell
TMIE200.
Composition comprises described " water-in-oil " emulsification system of 0.5 weight % to 10 weight % usually as defined above.
For 100 weight %, this inverse latex comprises 1% to 50 weight % water usually.
Above-mentioned oil phase from reversible inverse latex is made by following substances:
-mineral oil or mineral oil mixture, the stable hydrocarbon that it contains paraffinic hydrocarbons, isoparaffin or naphthenic hydrocarbon type has 0.7 to 0.9 density at ambient temperature and is higher than 180 ℃ boiling point, for example the Isopar of Exxon sale
TMM or Isopar
TML, Exxol
TMD100S or meet FDA21CFR172.878 and FR178.3620(a) mineral white oil of regulations, for example Marcol that also sells by Exxon
TM52 or Marcol
TM82;
-or synthetic oil or synthetic oil mixture, Parleam for example, particularly in France by Ets B.Hossow and Cie company with Parleam-Polysynlane
TMRun after fame and sell and at Michel and Irene Ash; Thesaurus of Chemical products, Chemise Publicit é Cos, Ince.1986 I volume, those that quote in the 211st page (ISBN0713136030); Poly decene; With the isohexadecane of label RN=93685-80-4 sign, it is to contain 97%C at least in Chemical Abstracts
16The C of isoparaffin
12, C
16And C
20The mixture of isoparaffin, wherein main component is 2,2,4,4,6,8,8-heptamethylnonane (RN=4390-04-9), it is sold by Bayer company in France; The Permethyl 99A. of selling by Bayer company in France;
-or vegetables oil or vegetable oil mixt, for example in Chemical Abstracts, use the squalane of label RN=111-01-3 sign, it is to contain more than 80 weight %2,6,10,15,19, the hydrocarbon mixture of 23-squalane, or the vegetables oil of ester or triglyceride level type, cocounut oil-octanoate/decylate for example, for example DUB that provides of Dubois company
TM810C, or jojoba oil;
-or these various oil in several mixture.
For 100 weight %, composition comprises the oil of 5% to 50 weight % usually as defined above.
According to a particular aspects, as the polyelectrolyte composition of the composition of theme of the present invention comprise the non-zero molar ratio by formula (I
1) the monomeric unit that produces of acid:
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-H (I
1)
Formula (I
1) being equivalent to the formula as defined above (I) that the representative of n wherein equals 1 number, described acid is the form of free or partially salinated.
According to another particular aspects, as the polyelectrolyte composition of the composition of theme of the present invention comprise the non-zero molar ratio by formula (I
1) acid and formula (I
2) the monomeric unit that produces of the mixture of acid:
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-H (I
1)
Formula (I
1) be equivalent to the formula as defined above (I) that the representative of n wherein equals 1 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
2)
Formula (I
2) being equivalent to the formula as defined above (I) that the representative of n wherein equals 2 number, described acid is the form of free or partially salinated, (I
1)/(I
2) mol ratio is greater than 1, and is more special in 1.5.
According to another particular aspects, as the polyelectrolyte composition of the composition of theme of the present invention comprise the non-zero molar ratio by formula (I
1) acid, formula (I
2) acid and formula (I
3) the monomeric unit that produces of the mixture of acid:
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-H (I
1)
Formula (I
1) be equivalent to the formula as defined above (I) that the representative of n wherein equals 1 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
2)
Formula (I
2) be equivalent to the formula as defined above (I) that the representative of n wherein equals 2 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
3)
Formula (I
3) being equivalent to the formula as defined above (I) that the representative of n wherein equals 3 number, described acid is the form of free or partially salinated, (I
1)/(I
2) mol ratio is greater than 1, and is more special in 1.5, and (I
2)/(I
3) mol ratio is greater than 1.5, and is more special in 2.
According to a particular aspects, for 100 moles of %, the anionoid polymerization electrolyte ingredient of inverse latex comprises as defined above:
The monomeric unit that the vinylformic acid by free or partially salinated of-90 moles of % to 99.5 mole of %, more special 95 moles of % to 99 mole of % produces;
The monomeric unit that the carboxylic acid of the formula by free or partially salinated of-0.5 mole of % to 10 mole of %, more special 1 mole of % to 5 mole of % (I) produces.
According to another particular aspects of the present invention, the anionoid polymerization ionogen is crosslinked as defined above.
Under one situation of back, linking agent is selected from diolefin or polyenic compounds especially, the most special two allyloxy acetate or its salt of being selected from, its sodium salt particularly, triallylamine or its salt, Viscoat 295, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diallyl urea or methylene-bis (acrylamide).
According to a particular aspects of the present invention, used linking agent is triallylamine or methylene-bis (acrylamide).
This linking agent uses with the molar ratio of representing with respect to used monomer of 0.005 mole of % to 1 mole of % usually.
According to another particular aspects of the present invention, composition also comprises " oil-in-water " emulsification system as defined above.
Described " oil-in-water (O/W) emulsification system " constituted or is made of surfactant mixture by single tensio-active agent, and condition is that described tensio-active agent or described mixture have the sufficiently high HLB value that is enough to cause water external emulsion.For example can mention:
The sorbitan ester of-ethoxylation, for example SEPPIC company is with Montanox
TM80 run after fame sell, by the sorbitan oleic acid ester of the many ethoxylations of 20 moles of ethylene oxide, or SEPPIC company is with Montanox
TM20 run after fame sell, by the sorbitan laurate esters of the many ethoxylations of 20 moles of ethylene oxide;
-with Simulsol
TMOL50 run after fame sell, by the Viscotrol C of the many ethoxylations of 40 moles of ethylene oxide;
-SEPPIC company is with Simulsol
TMThe run after fame ol é od é cylique alcohol of ten ethoxylations of selling of OC710;
-with Simulsol
TMThe run after fame dodecanol of seven ethoxylations of selling of P7; Or
-SEPPIC company is with run after fame sorbitan six oleic acid esters of many ethoxylations of selling of Simaline IE400.
When it also comprises " oil-in-water " emulsification system, as defined above composition be comprise usually 1 weight % to 15 weight % described " oil-in-water " emulsification system from reversible inverse latex form.
Composition of the present invention also can contain various additives, for example complexing agent or chain restriction agent.
According to another particular aspects of the present invention, its theme is a composition as defined above, and it comprises the described anionoid polymerization ionogen of 15 weight % to 60 weight %, preferred 25 weight % to 40 weight %.
According to another particular aspects of the present invention, its theme is a composition as defined above, and it comprises more than 60 weight % to 80 weight %, preferably more than the described anionoid polymerization ionogen of 60 weight % to 70 weight %.
The compound that n equals 1 formula (I) is known as 4-oxa--5-oxo-6-heptenoic acid or propenoic acid beta-carboxylic ethyl ester, is the commercially available prod.It identifies with label CAS=24615-84-7.
According to a further aspect in the invention, its theme is the method for compositions that preparation as above-mentioned aspect define in each, comprises the steps:
Step a),In this process, comprising emulsification in the oil phase of lipophilic described monomer and described optional additives at the aqueous solution that will comprise hydrophilic described monomer and described optional additives in the presence of the described invert emulsion system;
Step b),In this process, by introducing radical initiator and coinitiator randomly in the milk sap that forms when step a) finishes, initiated polymerization makes it carry out described composition with acquisition inverse latex form then.
As the process of step b) of the method for definition in, usually by generating bisulfite (HSO
3) the ionic oxidation/reduction is right, cumene hydroperoxide/Sodium Pyrosulfite (Na for example
2S
2O
5) right, or cumene hydroperoxide/thionyl chloride (SOCl
2) right, be less than or equal to initiated polymerization under 10 ℃ the temperature, if desired; be accompanied by photoreactive polymers; for example azo two (isopropyl cyanide), dilauroyl peroxide or Sodium Persulfate proceed to quasi-adiabatic the temperature more than or equal to 50 ℃ then, or are undertaken by controlled temperature.
According to a particular aspects, method also comprises as defined above
Step c), in this process, be to add to described oil-in-water emulsion
Step b)In the inverse latex that forms during end, to obtain described composition from reversible inverse latex form.
In the process of the step c) of method as defined above, be less than or equal to the interpolation of carrying out described oil-in-water emulsion system under 50 ℃ the temperature usually.
According to a particular aspects, also comprise as the method that defines
Step b 1 , in this process, if suitably implementing
Step c)Before, will available from
Step b)Inverse latex concentrate to obtain the described composition of spissated inverse latex form.
According to a particular aspects, method also comprises as defined above
Step c 1 , in this process, will available from
Step c)Concentrate to obtain spissated described composition from reversible inverse latex from reversible inverse latex form.
At the step b of method as defined above
1Or step c
1Process in, usually carry out concentrating of medium until reaching the anionoid polymerization ionogen as the desirable content in the composition of theme of the present invention by distillation.
According to a particular aspects, method also comprises as defined above
Step d), in this process, will available from
Step b)Inverse latex, available from
Step b1)Spissated inverse latex, available from
Step C)From reversible inverse latex or available from
Step c1)Spissated from reversible inverse latex spraying drying, to form the electrolytical powder of described anionoid polymerization.
Theme of the present invention also has straight chain or the crosslinked electrolytical powder of anionoid polymerization, it is characterized in that it is by method acquisition as defined above.
As the anionoid polymerization ionogen of theme of the present invention and comprise its inverse latex and be advantageously used for thickening material and/or emulsifying agent/stablizer in makeup or the pharmaceutical composition from reversible inverse latex.
Therefore, according on the other hand, theme of the present invention is the composition or the purposes of powder as defined above as defined above, as thickening material and/or the emulsifying agent in makeup or the pharmaceutical composition.
As the powder of theme of the present invention or randomly can be formulated in makeup or the pharmaceutical preparation (for example mousse, gel, washing lotion, spraying, shampoo, hair conditioner, handguard breast and health breast and sunscreen), be more typically in the care products from the composition of reversible inverse latex form.
Under the situation of hair treatment or maintenance, the form of the normally shampoo of this makeup or pharmaceutical composition, emulsion, microemulsion, special under the situation of hair conditioner, be transpirable emulsion form.
According to last aspect, theme of the present invention is makeup or pharmaceutical composition, it is characterized in that its contain the composition as defined above of significant quantity or as defined above powder as emulsifying agent and/or thickening material.
Term " significant quantity " is meant the part by weight of about 1 weight % to the composition as defined above of about 10 weight % and the about 0.2 weight % powder as defined above to about 5%.
The present invention of following embodiment illustration, but do not limit the present invention.
Embodiment A: with triallylamine crosslinked with acrylic acid homopolymer of sodium-salt form partially salinated
From reversible inverse latex (prior art)
Preparation from reversible inverse latex
-by mixing following material, the preparation oil phase:
261 gram Marcol
TM52,
15.5 gram Montane
TM80VG and
3.5 gram Montanox
TM81:3.5g.
-by introducing following material, the preparation water:
203 gram glacial acrylic acids,
188 grams contain the aqueous solution of 48 weight % sodium hydroxide,
0.45 gram Versenex
TM80,
0.77 the gram triallylamine makes weight reach 653 grams with deionized water then.
-water is introduced in the oil phase, and use Ultra Turrax
TMDevice carries out emulsification.
-in this system of stirring and after, it is cooled to 10 ℃ with the nitrogen bubbling, and to wherein adding 10 cubic centimetres at Marcol
TMThe solution that contains 0.268 weight % cumene hydroperoxide in 52 adds the aqueous solution that 20 grams contain 0.54 weight % Sodium Pyrosulfite then gradually.
-make the temperature in the reaction medium rise to 80 ℃, reaction was carried out 1 hour.With 30 gram Montanox
TM80 introduce in the final inverse latex of gained.
The viscosity analysis of the reversible inverse latex that derives from
3 weight % are from the viscosity of the water dispersion of reversible inverse latex: 55800mPas(Brookfield
TMRVT, axle 6, speed: 5 rev/mins).
Contain 0.1 weight % sodium-chlor and 3 weight % viscosity: 3200mPas(Brookfield from the water dispersion of reversible inverse latex
TMRVT, 3,5 rev/mins of axles).
Embodiment 1: with the crosslinked vinylformic acid/propenoic acid beta with the sodium-salt form partially salinated-carboxylic of triallylamine The multipolymer of ethyl ester is at Marcol TM In 52 from reversible inverse latex(composition 1)
Preparation from reversible inverse latex
-by mixing following material, the preparation oil phase:
261 gram Marcol
TM52,
15.5 gram Montane
TM80VG and
3.5 gram Montanox
TM81:3.5g.
-by introducing following material, the preparation water:
186 gram glacial acrylic acids,
17.3 the propenoic acid beta-carboxylic ethyl ester of gram, Bimax company is with Beta-C
TMThe sale of running after fame,
188 grams contain the aqueous solution of 48 weight % sodium hydroxide,
0.45 gram Versenex
TM80,
0.77 the gram triallylamine makes weight reach 653 grams with deionized water then.
-water is introduced in the oil phase, and use Ultra Turrax
TMDevice carries out emulsification.
-in this system of stirring and after, it is cooled to 10 ℃ with the nitrogen bubbling, and to wherein adding 10 cubic centimetres at Marcol
TMThe solution that contains 0.268 weight % cumene hydroperoxide in 52 adds the aqueous solution that 20 grams contain 0.54 weight % Sodium Pyrosulfite then gradually.
-make the temperature in the reaction medium rise to 80 ℃, reaction was carried out 1 hour.With 30 gram Montanox
TM80 introduce in the final inverse latex of gained.
The viscosity analysis of the reversible inverse latex that derives from
3 weight % are from the viscosity of the water dispersion of reversible inverse latex: 80400mPas(Brookfield
TMRVT, axle 6, speed: 5 rev/mins).
Contain 0.1 weight % sodium-chlor and 3 weight % viscosity: 5600mPas(Brookfield from the water dispersion of reversible inverse latex
TMRVT, 3,5 rev/mins of axles).
This analysis can confirm the thickening power of more strengthening from reversible inverse latex than embodiment A, and this is owing to there is the monomeric unit that is produced by propenoic acid beta-carboxylic ethyl ester.Also note that the slight improvement of salts contg.
Embodiment 2: with the crosslinked vinylformic acid/propenoic acid beta with the sodium-salt form partially salinated-carboxylic of triallylamine The multipolymer of ethyl ester in squalane from reversible inverse latex(composition 2)
This method is carried out as in Example 1, with Marcol
TM52 change Squalane into
TMVG.Obtain expection from reversible inverse latex.
Embodiment 3: with the crosslinked vinylformic acid/propenoic acid beta with the sodium-salt form partially salinated-carboxylic of triallylamine The multipolymer of ethyl ester is at Iso p Ar TM Among the M from reversible inverse latex(composition 3)
This method is carried out as in Example 1, with Marcol
TM52 change Isopar into
TMM.Obtain expection from reversible inverse latex.
Embodiment 4: with the crosslinked vinylformic acid/propenoic acid beta with the sodium-salt form partially salinated-carboxylic of triallylamine
The powder of the multipolymer of ethyl ester
By distill concentrate obtain among the last embodiment from reversible inverse latex, spraying drying then.
Example of formulations
Embodiment 5: protective skin cream
Embodiment 6: protective skin cream
Embodiment 7: must back cream
Prescription
Program: B is added among the A.
Embodiment 8: bright health breast
FORMULA
Program: C is added among the B, under 70 ℃ in A emulsification B, add down D and add E down at 60 ℃ then at 30 ℃.
Embodiment 9: the health breast
Prescription
Program: under about 75 ℃ in A emulsification B; Add C down at about 60 ℃, add D down at about 30 ℃ then.
Embodiment 10:O/W Cream
Prescription
Program: at about 75 ℃ B introduced among the A; Add C down at about 60 ℃, add D down at about 45 ℃ then.
Embodiment 11: the sun protection gel of non-greasy
Prescription
Program: B is introduced among the A; Add C, D, E then then.
Embodiment 12: sunscreen
Prescription
Program: under 75 ℃ in A emulsification B, add down C at about 60 ℃ then, add D down at about 30 ℃ then, if necessary, regulate pH.
Embodiment 13: massage gel
Prescription
Program: B is added among the A; Then C is added in this mixture, then D.
Embodiment 14: massage gel
Prescription
Program: preparation A; Add B, C, D then then.
Embodiment 15: glossy gel
Prescription
Program: preparation A; Add B, C, D then then.
Embodiment 16: the health breast
Prescription
Program: at about 75 ℃ of following fusion A.Under 75 ℃ in A emulsification B, add down C, D then at about 60 ℃ then.
Embodiment 17: the makeup removing breast that contains sweet almond oil
Prescription
Embodiment 18: oiliness skin moisturizer
Prescription
Embodiment 19: alcohol-free releiving must back cream
Prescription
Embodiment 20: the breast frost that contains AHA that responsive skin is used
Prescription
Embodiment 21: the care products of releiving after the solarization
Prescription
Embodiment 22: the makeup removing breast
Prescription
Embodiment 23: the health breast
Prescription
Embodiment 24: the emulsion under alkaline pH
Embodiment 25: foundation emulsion
Prescription
Embodiment 26: sunscreen
Prescription
Embodiment 27: the eye gel
Prescription
Embodiment 28: disposable care composition
Prescription
Embodiment 29: slim gel
Embodiment 30: alcohol-free releiving must back cream
Prescription
Embodiment 31: clearly must the back gel
Prescription
Embodiment 32: oiliness skin nursing product
Prescription
Embodiment 33: the breast frost that contains AHA
Prescription
Embodiment 34: the black product of U.S. of the non-greasy of face and health
Prescription
Prescription
Embodiment 36: facial sun-proof nursing product
Prescription
Embodiment 37: the U.S. black emulsion of no Exposure to Sunlight
Prescription
Embodiment 38: glossy gel
Embodiment 39: slim gel
Embodiment 40: the makeup removing breast
Embodiment 41: sunscreen
Embodiment 42: the mixed skin nursing gel
Embodiment 43: fragrance health film
Embodiment 44: the breast frost that contains VITAMIN
Embodiment 45: the resistance to compression hair products
Prescription
Phase A
Water: qs100%
Xanthan gum: 0.50%
Phase B
Sepicap
TM MP: 3.00%
Phase C
Composition 1:4.00%
Phase D
Program: with deflocculator xanthan gum is dispersed in the water.Add Sepicap then
TMMP, composition 1 then; It is disperseed, add the composition of phase D then.
Embodiment 46: the white film of regeneration breast of pressurized and embrittlement hair
Prescription
Phase A
Phase B
Water: q.s.100%
Phase C
Sepicap
TM MP: 3.00%
Sepicide
TM HB: 0.30%
Sepicide
TM CI: 0.20%
Program: at 75 ℃ of following fusion phase A.Phase B is heated to 75 ℃.Emulsification A in B.Under about 40 ℃, introduce the composition of phase C.
Embodiment 47: purify facial gel
Prescription
Phase A
Montaline
TM C 40: 7.00%
Pearlescent base 2078: 5.00%
Composition 1:2.00%
Phase B
Water: q.s.100%
Embodiment 48: painted shampoo
Prescription
Phase A
Phase B
Tinting material qs
Water q.s.100%
Embodiment 49: shampoo
Embodiment 50: the shampoo of protecting and releive
Embodiment 51: disposable protective agent; The resistance to compression hair products
Montanov
TM68 (cetearyl glucoside) are the self-emulsifying compositions described in WO92/06778, are sold by SEPPIC company.
Montanov
TM82 are based on the emulsifying agent of the pure and mild cocounut oil acyl of cetearyl alcohol glucoside.
Montanov
TMThe 202nd, the APG/ Fatty Alcohol(C12-C14 and C12-C18) composition described in WO98/47610 is sold by SEPPIC company.
Micropearl
TMLM is the mixture of the squalane of SEPPIC company sale, poly-(methyl methacrylate) and menthol.
Micropearl
TMM100 be Matsumo company sell have a very ultrafine powder of softish sense of touch and photoextinction.
Micropearl
TMSQL is the mixture that contains the particulate of the squalane that discharges under massage effect; It is sold by Matsumo company.
Sepicide
TMHB is the mixture of phenoxyethyl alcohol, methyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, propylparaben and butyl p-hydroxybenzoate, and it is the sanitas that SEPPIC company sells.
Sepicide
TMCI, the imidazolidine urea is the sanitas that SEPPIC company sells.
Pemulen
TMTR is the acrylate copolymer that Goodrich sells.
Simulsol
TMThe 165th, the self-emulsifying stearin that SEPPIC company sells.
Lanol
TM14M and Lanol
TMS is the consistency factor that SEPPIC company sells.
Lanol
TM84D is the oxysuccinic acid dioctyl ester that SEPPIC company sells.
Lanol
TMThe 99th, the isononyl isononanoate that SEPPIC company sells.
Lanol
TM37T is the triheptin that SEPPIC company sells.
Lanol
TMP is the additive with stabilization that SEPPIC company sells.
Lanol
TMThe 1688th, the emollient ester that SEPPIC company sells with the effect of deoiling.
Lanol
TMThe 2681st, lauric alcohol octanoate/decylate mixture that SEPPIC company sells.
Monteine
TMCA is the wetting Agent for Printing Inks that SEPPIC company sells.
Schercemol
TMOP is the emollient ester with the effect of deoiling.
Parsol
TMMCX is the p-methoxycinnamic acid monooctyl ester that Givaudan company sells.
Sepiperl
TMN is the pearling agent that SEPPIC company sells, based on the mixture of alkyl polyglucoside, for example those described in the WO95/13863.
Solagum
TML is the carrageenin that SEPPIC company sells.
Marcol
TMThe 82nd, the whiteruss that Exxon company sells.
Parsol
TMNOX is the sun-screening agent that Givaudan company sells.
Eusolex
TMThe 4360th, the sun-screening agent that Merck company sells.
Dow Corning
TM245Fluid is the cyclomethicone that Dow Corning company sells.
Lipacide
TMPVB is the acidylate hydrolyzed wheat protein product that SEPPIC company sells.
Sepicontrol
TMA5 is the mixture of decoyl glycine, sarkosine and the Cortex Cinnamomi extract of the sale of SEPPIC company, for example those described in the International Patent Application PCT/FR98/01313 that submitted on June 23rd, 1998.
Capigel
TMThe 98th, the acrylic copolymer that SEPPIC company sells.
Commodity used among the embodiment are defined as follows:
Montaline
TM(the cocamoniumcarbamoyl chloride) that C40:SEPPIC sells.
Sepiperl
TM(the cocoyl glucoside/cocoyl alcohol) that N:SEPPIC sells.
Amonyl
TM(Quaternium82) that DM:SEPPIC sells.
Sepicap
TM(the cocoyl amino acid sodium/dimethicone copolyol panthenol base potassiumphosphate) that MP:SEPPIC sells
Simulsol
TMThe 1293rd, the ethoxylation index that SEPPIC company sells equals 40 the hydrogenation and the Viscotrol C of ethoxylation.
Ketrol
TMT is the xanthan gum that Kelco company sells.
DC1501 is the D5 of Dow Chemical company sale and the mixture of dimethiconol.
Claims (14)
1. the composition of inverse latex form, it comprises oil phase, water and at least a invert emulsion system, it is characterized in that it comprises straight chain, side chain or crosslinked anionoid polymerization ionogen, and described anionoid polymerization ionogen comprises:
A) monomeric unit that produces of the vinylformic acid by the form of free or partially salinated of non-zero molar ratio and
B) the non-zero molar ratio by the acid of formula (I) or the monomeric unit that produces by the mixture of the acid of formula (I)
CH
2=CH-C(=O)-O-[CH
2-CH
2-C(=O)-O]
n-H (I)
Wherein n represents more than or equal to 1 and is less than or equal to 5 number, and described acid is the form of free or partially salinated.
2. the composition described in claim 1, wherein for 100 moles of %, described anionoid polymerization ionogen comprises:
The monomeric unit that the vinylformic acid by free or partially salinated of-90 moles of % to 99.5 mole of %, more special 95 moles of % to 99 mole of % produces;
The monomeric unit that the carboxylic acid of the formula by free or partially salinated of-0.5 mole of % to 10 mole of %, more special 1 mole of % to 5 mole of % (I) produces.
3. the composition described in claim 1 or 2, wherein said anionoid polymerization ionogen comprise the non-zero molar ratio by formula (I
1) acid and formula (I
2) the monomeric unit that produces of the mixture of acid:
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-H (I
1)
Its Chinese style (I
1) be equivalent to the formula as defined above (I) that the representative of n wherein equals 1 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
2)
Its Chinese style (I
2) be equivalent to the representative of n wherein and equal 2 number formula (I) as defined above,
Described acid is the form of free or partially salinated, (I
1)/(I
2) mol ratio is greater than 1, and is more special in 1.5.
4. the composition described in claim 2, wherein said anionoid polymerization ionogen comprise the non-zero molar ratio by formula (I
1) acid, formula (I
2) acid and formula (I
3) the monomeric unit that produces of the mixture of acid:
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-H (I
1)
Its Chinese style (I
1) be equivalent to the formula as defined above (I) that the representative of n wherein equals 1 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
2)
Its Chinese style (I
2) be equivalent to the formula as defined above (I) that the representative of n wherein equals 2 number,
CH
2=CH-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-O-CH
2-CH
2-C(=O)-OH (I
3)
Its Chinese style (I
3) be equivalent to the formula as defined above (I) that the representative of n wherein equals 3 number,
Described acid is the form of free or partially salinated, (I
1)/(I
2) mol ratio is greater than 1, and is more special in 1.5, and (I
2)/(I
3) mol ratio is greater than 1.5, and is more special in 2.
5. as the composition of claim 1 to 4 described in each, wherein the anionoid polymerization ionogen is crosslinked as defined above.
6. as the composition of claim 1 to 5 described in each, it comprises the described anionoid polymerization ionogen of 15 weight % to 80 weight %.
7. as the composition of claim 1 to 6 described in each, it also comprises " oil-in-water " emulsification system.
8. preparation comprises the steps: as the method for compositions of claim 1 to 7 described in each
Step a), in this process, comprising emulsification in the oil phase of lipophilic described monomer and described optional additives at the aqueous solution that will comprise hydrophilic described monomer and described optional additives in the presence of the described invert emulsion system;
Step b), in this process, by introducing radical initiator and coinitiator randomly in the milk sap that forms when step a) finishes, initiated polymerization makes it carry out described composition with acquisition inverse latex form then.
9. the method described in claim 8, it also comprises
Step c), in this process, be to add to described oil-in-water emulsion
Step b)In the inverse latex that forms during end, to obtain described composition from reversible inverse latex form.
10. the method described in claim 8 or 9, it also comprises
Step b 1 , in this process, if suitably implementing
Step c)Before, will available from
Step b)Inverse latex concentrate to obtain the described composition of spissated inverse latex form.
11. the method described in claim 10, it also comprises
Step c 1 , in this process, will available from
Step c)Concentrate to obtain spissated described composition from reversible inverse latex from reversible inverse latex form.
12. as the method for claim 8 to 11 described in each, it also comprises
Step d), in this process, will available from
Step b)Inverse latex, available from
Step b1)Concentrated inverse latex, available from
Step c)From reversible inverse latex or available from
Step c1)Concentrate from reversible inverse latex spraying drying, to form the electrolytical powder of described anionoid polymerization.
13. as the composition of claim 1 to 7 described in each or the purposes of the powder described in claim 13, as thickening material and/or the emulsifying agent in makeup or the pharmaceutical composition.
14. makeup or pharmaceutical composition, it is characterized in that its contain significant quantity as the composition of claim 1 to 7 described in each or as powder by the acquisition of the method as claim 12 described in as emulsifying agent and/or thickening material.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1059944 | 2010-11-30 | ||
FR1059944A FR2968007B1 (en) | 2010-11-30 | 2010-11-30 | NOVEL POLYMERIC THICKENER FREE FROM ANY ACRYLAMIDO FRAGMENT, PROCESS FOR THEIR PREPARATION AND COMPOSITION CONTAINING THE SAME. |
PCT/FR2011/052648 WO2012072911A1 (en) | 2010-11-30 | 2011-11-16 | Novel polymeric thickening agent free of acrylamide fragments, method for the preparation thereof, and composition containing same |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103228725A true CN103228725A (en) | 2013-07-31 |
CN103228725B CN103228725B (en) | 2016-04-06 |
Family
ID=43735157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180057532.3A Expired - Fee Related CN103228725B (en) | 2010-11-30 | 2011-11-16 | Without the novel polymeric thickening material of acrylamide fragment, its preparation method and the composition containing this polymeric viscosifier |
Country Status (7)
Country | Link |
---|---|
US (1) | US9144610B2 (en) |
EP (1) | EP2646510B1 (en) |
JP (1) | JP5917550B2 (en) |
KR (1) | KR20130141558A (en) |
CN (1) | CN103228725B (en) |
FR (1) | FR2968007B1 (en) |
WO (1) | WO2012072911A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115003750A (en) * | 2019-12-09 | 2022-09-02 | 化工产品开发公司Seppic | Inverse latex for cosmetic compositions combining a specific sequestering agent and a polyelectrolyte with weak acid functions |
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US10773973B2 (en) * | 2013-03-08 | 2020-09-15 | Ecolab Usa Inc. | Enhanced foam removal of total suspended solids and multiply charged cations from aqueous or aqueous/oil mixed phase via increased viscoelasticity |
US10435308B2 (en) | 2013-03-08 | 2019-10-08 | Ecolab Usa Inc. | Enhanced foam fractionation of oil phase from aqueous/oil mixed phase via increased viscoelasticity |
FR3104166B1 (en) * | 2019-12-09 | 2021-12-10 | Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic | Detergent composition comprising an inverse latex combining a particular sequestering agent and a polyelectrolyte comprising a weak acid function |
WO2022248317A1 (en) | 2021-05-26 | 2022-12-01 | Rhodia Operations | COMPOSITION FOR PAINTING/COATING APPLICATIONS CONTAINING A PARTICULAR COPOLYMER DISPERSANT WITH AT LEAST ONE β-CARBOXYETHYL ACRYLATE MONOMER |
WO2022248591A1 (en) | 2021-05-26 | 2022-12-01 | Rhodia Operations | Agrochemical composition containing a particular copolymer dispersant with at least one β-carboxyethyl acrylate monomer |
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FR2762317B1 (en) | 1997-04-21 | 1999-07-09 | Seppic Sa | COMPOSITION BASED ON ALKYLPOLYGLYCOSIDES AND FATTY ALCOHOLS AND USES THEREOF |
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FR2856691B1 (en) * | 2003-06-26 | 2005-08-26 | Seppic Sa | NOVEL POWDER POLYMER, PROCESS FOR PREPARING THE SAME, AND USE AS THICKENING |
DE102009014877A1 (en) | 2009-03-25 | 2009-09-24 | Clariant International Ltd. | New polymer comprising nitrogen containing-, carbonyl containing-, and crosslinking structural units useful e.g. as thickener and emulsifier, and cosmetic, dermatological or pharmaceutical composition |
-
2010
- 2010-11-30 FR FR1059944A patent/FR2968007B1/en not_active Expired - Fee Related
-
2011
- 2011-11-16 US US13/878,604 patent/US9144610B2/en not_active Expired - Fee Related
- 2011-11-16 JP JP2013541401A patent/JP5917550B2/en active Active
- 2011-11-16 WO PCT/FR2011/052648 patent/WO2012072911A1/en active Application Filing
- 2011-11-16 KR KR1020137013715A patent/KR20130141558A/en not_active Application Discontinuation
- 2011-11-16 EP EP11796749.7A patent/EP2646510B1/en active Active
- 2011-11-16 CN CN201180057532.3A patent/CN103228725B/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
FR2968007B1 (en) | 2014-03-14 |
EP2646510A1 (en) | 2013-10-09 |
JP2013545851A (en) | 2013-12-26 |
KR20130141558A (en) | 2013-12-26 |
US20130190410A1 (en) | 2013-07-25 |
CN103228725B (en) | 2016-04-06 |
JP5917550B2 (en) | 2016-05-18 |
WO2012072911A1 (en) | 2012-06-07 |
US9144610B2 (en) | 2015-09-29 |
EP2646510B1 (en) | 2015-03-04 |
FR2968007A1 (en) | 2012-06-01 |
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